CN1444103A - Optical photoresist stripping composition and cleaning composition - Google Patents

Optical photoresist stripping composition and cleaning composition Download PDF

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Publication number
CN1444103A
CN1444103A CN03120076A CN03120076A CN1444103A CN 1444103 A CN1444103 A CN 1444103A CN 03120076 A CN03120076 A CN 03120076A CN 03120076 A CN03120076 A CN 03120076A CN 1444103 A CN1444103 A CN 1444103A
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Prior art keywords
methyl amine
composition
amine compound
oxygen methyl
photoresist lift
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CN03120076A
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CN1312535C (en
Inventor
池本一人
山本良亮
吉田宽史
丸山岳人
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Mitsubishi Gas Chemical Co Inc
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Mitsubishi Gas Chemical Co Inc
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Priority claimed from JP2002066529A external-priority patent/JP4035701B2/en
Priority claimed from JP2002183711A external-priority patent/JP4061475B2/en
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/42—Stripping or agents therefor
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/32—Organic compounds containing nitrogen
    • C11D7/3227—Ethers thereof
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/42—Stripping or agents therefor
    • G03F7/422—Stripping or agents therefor using liquids only
    • G03F7/425—Stripping or agents therefor using liquids only containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/42—Stripping or agents therefor
    • G03F7/422—Stripping or agents therefor using liquids only
    • G03F7/426—Stripping or agents therefor using liquids only containing organic halogen compounds; containing organic sulfonic acids or salts thereof; containing sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/14—Hard surfaces
    • C11D2111/22—Electronic devices, e.g. PCBs or semiconductors

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
  • Cleaning Or Drying Semiconductors (AREA)
  • Detergent Compositions (AREA)

Abstract

The photoresist stripping composition of the present invention contains at least one oxymethylamine compound represented by the following formula 1: wherein R<1 >to R<3 >are as defined in the specification. Of the oxymethylamine compound of the formula 1, the compound represented by the following formula 7: wherein R<2 >to R<5 >and n are as defined in the specification, is a novel compound.

Description

Photoresist lift off composition and cleaning combination
Background of invention
1. invention field
Photoresist has been used in the photoetching process production run of multiple element, and these elements comprise integrated circuit such as LC and LSI, display element such as LCD and EL element, printed circuit board, microcomputer, DNA chip and microdevice (plant).Particularly, the present invention relates to be used for removing the photoresist lift off composition of photoresist from the various substrates that have photoresist.
Because the alkalescence and the nucleophilicity of aminated compounds have been used to clean integrated circuit, liquid crystal display cells and printed circuit board, and have been used to remove the photoresist that is coated onto on these element substrates.The invention still further relates to a kind of new be used for this classification optimum amines, its preparation method, and the cleaning combination and the photoresist lift off composition that contain this new amines.
2. DESCRIPTION OF THE PRIOR ART
Usually alkaline stripping composition is used to remove photoresist.For example can be by Tokyo Oka Co., the TOK106 that Ltd. obtains contains alkanolamine and dimethyl sulfoxide, can be by EKC TechnologyCo., the EKC265 that Ltd. obtains contains alkanolamine, azanol, catechol and water.U.S. Patent No. 4,276,186 disclose a kind of composition that contains N-Methyl pyrrolidone and monoethanolamine, and open communique (laid open) No.4-289866 of Japanese patent application discloses a kind of composition that contains alkanolamine and azanol.
As " industrial organic chemistry " (Industrial Organic Chemistry) (the 4th edition, the 175th page, Tokyo Kagaku Dojin Co., Ltd.Sakiyama Mitsuaki compiles) described in, can synthesize these alkanolamines by corresponding alkylene oxide and ammonia react.These alkanols are very cheap, because can prepare by simple method.But use alkanolamine can not reach now separately, be specially the requirement of finishing and short-term processing procedure in semiconductor element and LCD panel production run.In order to reach this requirement, open communique No.11-194505 of Japanese patent application and No.6-266119 disclose the composition that contains azanol.The described compositions display that contains azanol high resist removal effect.But the shortcoming of azanol is easy decomposition, and this makes its purification be difficult to obviously increase its cost.
For not having these shortcomings and can effectively improve the compound of resist removal effect, the open communique No.2000-250230 of Japanese patent application discloses methylol amine.Although compare with azanol, methylol amine is stable, and wherein contained hydroxyl has increased its viscosity.Recently, be used for the semiconductor element of SIC (semiconductor integrated circuit) and liquid crystal display cells by various manufacture of materials, this requires the resist stripping composition that various substrate materials are not all had corrosive attack.
Summary of the invention
The objective of the invention is to solve the problem of peeling off at resist in the prior art, and a kind of photoresist lift off composition is provided, and described photoresist lift off composition can be removed at an easy rate at short notice at low temperatures and be coated in on-chip photoresist layer, the photoresist residue after etching after remaining photoresist layer, the polishing after etching.Another object of the present invention provides a kind of photoresist lift off composition, described photoresist lift off composition can be removed photoresist layer and photoresist residue under the situation of not corroding processed substrate material, thereby can finishing and produce high-precision circuit.Another purpose of the present invention provides a kind ofly utilizes described photoresist lift off composition to remove the method for photoresist.A further object of the present invention provides a kind of new amines that is suitable as the photoresist lift off composition component.
Because the result of broad research, the inventor have been found that contain the (alkoxymethyl)-2 ylamine compounds composition at low temperatures at short notice, remove easily photoresist layer and after the etching on substrate remaining photoresist residue, and the remaining photoresist residue afterwards of the polishing etching after.The inventor finds that also this composition removes photoresist under the situation of not corroding conductor material and insulation course, thereby can carry out finishing and high-precision circuit is provided.The inventor finds that also new quilt contains the alkoxyamine compound (hereinafter referred to as " new oxygen methyl amine compound ") that the substituting group of ehter bond replaces and can effectively remove photoresist.
Brief Description Of Drawings
Fig. 1 is the cross sectional representation that is used for the test substrate of embodiment 18-21 and 25-29 and comparative example 5-6 and 8-10, and this figure has provided polysilicon (polysilicon) layer after partly exposing; And
Fig. 2 is (2-methoxyl-2-ethoxy ethoxy methyl) diethylamide of preparation among the embodiment 22 1H-NMR figure.
The detailed description of invention
Photoresist lift off composition of the present invention contains at least a oxygen methyl amine compound ((alkoxymethyl)-2 ylamine compounds+new oxygen methyl amine compound), and this compound is specifically by following general formula 1 expression:
R wherein1For alkyl, hydroxyalkyl, aryl, acyl group, alkoxyalkyl, aminoalkyl or contain The substituting group that ehter bond is arranged; R2Be hydrogen, alkyl, acyl group, hydroxyalkyl, aryl, pi-allyl, ammonia Alkyl, alkoxyalkyl, hydroxyl or amino; R3Be hydrogen, alkyl, acyl group, hydroxyalkyl, virtue Base, pi-allyl, aminoalkyl, alkoxyalkyl, hydroxyl or amino. Work as R2And R3When being the group with 1-8 carbon atom, R2And R3And and R2And R3The N that links to each other together can shape Circlewise structure such as morpholine ring, piperidine ring and piperazine ring. R wherein1For containing the substituting group of ehter bond The oxygen methyl amine compound of general formula 1 be new. At R1To R3Definition in, use separately Or be used for the compound word and reach " aminoalkyl " such as " hydroxyalkyl ", " alkoxyalkyl " Term " alkyl " comprises the straight chained alkyl with 1-14 carbon atom or has 3-14 carbon former The branched alkyl of son. Acyl group preferably has 2-6 carbon atom. The example of aryl is phenyl and naphthalene Base.
Described oxygen methyl amine compound comprises disclosed basic structure by following general formula 6 expressions among the open communique No.2000-250230 of Japanese patent application:
Figure A0312007600082
As the discovery on basis of the present invention is the adverse effect that the oxygen methyl amine compound of general formula 1 can effectively be eliminated the hydroxyl of methylol amine.
R wherein 1For alkyl, hydroxyalkyl, alkoxyalkyl or the oxygen methyl amine compound that contains the substituent general formula 1 of ehter bond are preferred, this is because they obtain and preparation easily easily.The boiling point of described oxygen methyl amine compound is preferably 40 ℃ or higher.If be lower than 40 ℃, then described oxygen methyl amine compound may be escaped and be changed the chemical composition of photoresist lift off composition.
Be used for oxygen methyl amine compound of the present invention and at least one oxygen methyl amine structure (＞N-CH arranged at a molecule 2-O-R 1), but in a molecule, have two or more oxygen methyl amine structures not have negative effect.Described oxygen methyl amine compound can be the form of mineral acid or organic acid salt.
(alkoxymethyl)-2 ylamine compounds (the oxygen methyl amine compound of general formula 1, wherein R 1Be the group except that the substituting group that contains ehter bond) comprise (butoxymethyl) diethylamine, (methoxy) diethylamine, (methoxy) dimethylamine, (butoxymethyl) dimethylamine, (isobutoxy methyl) dimethylamine, N-(methoxy) morpholine, N-(butoxymethyl) morpholine, N-(methoxy) piperidines, N-(butoxymethyl) piperidines, two (methoxy) aminoethane, two (methoxy) aminomethane, two (butoxymethyl) aminoethane, two (butoxymethyl) aminomethane, two (methoxy) ethylaminoethanol, two (butoxymethyl) ethylaminoethanol, two (methoxy) amino ethoxy ethanol, two (butoxymethyl) amino ethoxy ethanol, two (methoxy) amino ethoxy methane, methyl (methoxy) aminoethane, methyl (methoxy) ethylaminoethanol, methyl (butoxymethyl) ethylaminoethanol, two (methoxy) aminopropanol, two (butoxymethyl) aminopropanol, the amino isopropyl alcohol of two (methoxies), the amino isopropyl alcohol of two (butoxymethyl), N, N-two (methoxy)-N ', N '-dimethyl ethylene diamine, N, N '-two (methoxy) piperazine, two (butoxymethyl) piperazine, (methoxy) diethanolamine and (hydroxyethyl oxygen methyl) diethylamide.Described (alkoxymethyl)-2 ylamine compounds is not limited to above listed those, can be included in the compound that at least one oxygen methyl amine structure is arranged in the molecule.
For the preparation method of amines with general formula 6 structures, G.M.Robinson, R.Robinson, J.Chem.Soc., 123,523 (1923) have reported wherein R 1Preparation for the (alkoxymethyl)-2 ylamine compounds of the general formula 1 of alkyl.Although for strengthening the resist removal effect is that effectively the solubleness of this amines in water is not enough, and scent of.In order to improve the solubleness in water and to reduce smell and the result of study of the MOLECULE DESIGN of carrying out shows that the inventor has been found that new wherein R 1For the oxygen methyl amine compound of the substituent general formula 1 that contains ehter bond is effective for this improvement.
Described new oxygen methyl amine compound is preferably by following general formula 7 expressions:
R wherein 2And R 3As hereinbefore defined; R 4For having 1-8 carbon atom, being preferably the straight or branched alkyl of 1-4 carbon atom; R 5For having 1-4 carbon atom, being preferably the straight or branched alkylidene of 2 or 3 carbon atoms; N is 1-4, be preferably 1 or 2 integer.When n is the integer of 2-4, two or more R 5Group can be identical or different.
In order further to improve the solubleness in water, the ether-containing key substituting group with a plurality of ehter bonds by following general formula 2 expressions is preferred below:
-CH 2-CH 2-O-CH 2-CH 2-O-R 4 (2)
R wherein 4As hereinbefore defined.
The more preferably following ether-containing key substituting group of deriving and obtaining by safer propylene glycol, this substituting group is represented by following general formula 3:
R wherein 4As hereinbefore defined.
Particularly preferred wherein R 1For the compound of the substituent general formula 1 of ether-containing key is a new oxygen methyl amine compound by following general formula 4 expressions: And by the new oxygen methyl amine compound of following general formula 5 expressions:
R wherein 1For the new oxygen methyl amine compound of the substituent general formula 1 that contains ehter bond can be according to G.M.Robinson, R.Robinson, J.Chem.Soc., the method described in 123,523 (1923) is by amines, formaldehyde and to contain the alcohol of ehter bond synthetic.In the method, oxygen methyl amine compound is by synthetic from the alcoholic extract hydroxyl group of the methylol amine of amines and formaldehyde reaction and the dehydration that contains between the alcoholic extract hydroxyl group of alcohol of ehter bond.
For the alcohol that contains ehter bond, glycol ethers is because its acquisition and preferred use easily.Its example comprises ethylene glycol monomethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, TC, diethylene glycol single-butyl ether, diethylene glycol, triethylene glycol, triethylene glycol monomethyl ether, triethylene glycol list ethylether, triethylene glycol single-butyl ether, propylene glycol monomethyl ether, propylene glycol list ethylether, propylene glycol single-butyl ether, DPGME, dihydroxypropane single-ethyl ether and dipropylene glycol single-butyl ether.
Initial amines is not particularly limited, and can have specific limited ground to use primary amine and secondary amine.Method such as extraction, rectifying and recrystallization that described amines utilization is generally used for organic compound carry out purifying.
Because oxygen methyl amine compound plays amines, it can be used for cleaning the semiconductor element that wherein uses amines usually.R wherein 1Can be used for wherein using usually the cleaning of ether compound for the oxygen methyl amine compound of the substituent general formula 1 that contains ehter bond.Has ehter bond simultaneously and amino oxygen methyl amine compound is effective especially for cleaning semiconductor, simultaneously because its low-corrosiveness also is effective for the finishing of semiconductor element.
Described oxygen methyl amine compound is effective especially for removing resist.Its reason it be unclear that, but can think following reason.Remove-O-R by oxygen methyl amine compound 1After aminomethyl group link to each other with the phenolic hydroxyl group of photoresist, the solubleness that this has increased photoresist is removed resist easily.When the alkaline compositions of mentioning below exists,, the solubleness of photoresist is further increased, thereby further improved the removal ability of resist owing to promoted the decomposition of photoresist.
Photoresist lift off composition of the present invention and cleaning combination can contain alkali compounds, organic solvent, antiseptic and surfactant, and these materials can be used singly or in combination.
The example of alkali compounds comprises primary alkyl amine such as methylamine, ethamine, the n-propylamine, isopropylamine, the n-butylamine, sec-butylamine, isobutyl amine, tert-butylamine, amylamine, the 2-aminopentane, the 3-aminopentane, 1-amino-2-methyl butane, 2-amino-2-methyl butane, 3-amino-2-methyl butane, 4-amino-2-methyl butane, hexylamine, 5-amino-2-methyl amylamine, heptyl amice, octylame, nonyl amine, decyl amine, undecyl amine, lauryl amine, tridecyl amine, tetradecylamine, pentadecyl amine, hexadecylamine, heptadecyl amine and octadecylamine; Secondary alkyl amine such as dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, dibutylamine, diisobutyl amine, two sec-butylamine, di-t-butyl amine, diamylamine, dihexylamine, two heptyl amices, dioctylamine, nonyl amine, didecylamine, Methylethyl amine, methyl-propyl amine, isopropyl methyl amine, methyl butyl amine, methyl-isobutyl amine, the methyl sec-butylamine, methyl tertbutyl amine, methyl amyl amine, the methyl isoamylamine, ethyl propyl amine, the ethyl isopropylamine, N-Ethylbutylamine, the ethyl isobutylamine, the ethyl sec-butylamine, ethyl tert-butyl amine, the ethyl isoamylamine, propyl group butylamine and propyl group isobutylamine; Tertiary amine such as Trimethylamine, triethylamine, tripropylamine, tri-butylamine, three amylamines, dimethylethyl amine, methyl diethylamide and methyl dipropylamine; Alkanolamine such as monoethanolamine, the N-methylethanolamine, the N-ehtylethanolamine, N-propyl group monoethanolamine, the N-butylethanolamine, diethanolamine, isopropanolamine, N-methyl isopropyl hydramine, N-ethyl isopropanolamine, N-propyl group isopropanolamine, 2-aminopropane-1-alcohol, N-methyl-2-aminopropane-1-alcohol, N-ethyl-2-aminopropane-1-alcohol, 1-aminopropane-3-alcohol, N-methyl isophthalic acid-aminopropane-3-alcohol, N-ethyl-1-aminopropane-3-alcohol, 1-butylamine-2-alcohol, N-methyl isophthalic acid-butylamine-2-alcohol, N-ethyl-1-butylamine-2-alcohol, 2-butylamine-1-alcohol, N-methyl-2-butylamine-1-alcohol, N-ethyl-2-butylamine-1-alcohol, 3-butylamine-1-alcohol, N-methyl-3-butylamine-1-alcohol, N-ethyl-3-butylamine-1-alcohol, 1-butylamine-4-alcohol, N-methyl isophthalic acid-butylamine-4-alcohol, N-ethyl-1-butylamine-4-alcohol, 1-amino-2-methyl propane-2-alcohol, 2-amino-2-methyl propane-1-alcohol, 1-aminopentane-4-alcohol, 2-amino-4-methylpentane-1-alcohol, 2-aminohexane-1-alcohol, the amino heptane of 3--4-alcohol, 1-amino-octane-2-alcohol, 5-amino-octane-4-alcohol, 1-aminopropane-2, the 3-glycol, 2-aminopropane-1, the 3-glycol, three (oxygen methyl) aminomethane, 1,2-diaminopropanes-3-alcohol, 1, the pure and mild 2-of 3-diaminopropanes-2-(2-amino ethoxy) ethanol, polyamines such as ethylene diamine, trimethylene diamine, the trimethylene diamines, tetra-methylenedimine, 1, the 3-diaminobutane, 2, the 3-diaminobutane, five methylene diamine, 2,4-diamido pentane, hexamethylene diamine, the heptamethylene diamines, eight methylene diamine, nine methylene diamine, N-methyl ethylene diamine, N, N-dimethyl ethylene diamine, the trimethyl ethylene diamine, N-ethyl ethylene diamine, N, N-diethyl ethylene diamine, the triethyl ethylene diamine, 1,2,3-triamido propane, hydrazine, three (2-amino-ethyl) amine, four (amino methyl) methane, diethylene triamine, trien, tetren, seven ethylidene, eight amine, nine ethylidene, ten amine and diaza-bicyclo undecylene; Hydroxylamine compound such as azanol, N-methyl hydroxylamine, N-ethyl azanol, N, N-diethyl hydroxylamine and O-methyl hydroxylamine; Cyclammonium such as pyrroles, the 2-methylpyrrole, the 3-methylpyrrole, the 2-N-ethyl pyrrole N-, the 3-N-ethyl pyrrole N-, 2, the 3-dimethyl pyrrole, 2, the 4-dimethyl pyrrole, 3, the 4-dimethyl pyrrole, 2,3,4-trimethyl pyrroles, 2,3,5-trimethyl pyrroles, the 2-pyrrolin, the 3-pyrrolin, pyrrolidine, the 2-crassitude, the 3-crassitude, pyrazoles, imidazoles, 1,2,3,-triazole, 1,2,3, the 4-tetrazolium, piperidines, pipecoline, the 3-methyl piperidine, the 4-methyl piperidine, 2, the 4-lupetidine, 2, the 6-lupetidine, 3, the 5-lupetidine, piperazine, the 2-methyl piperazine, 2, the 5-lupetazin, 2,6-lupetazin and morpholine; And tetraethanolammonium hydroxide such as tetraethyl ammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium, hydrogen chloride, acetyl group hydrogen chloride.Described oxygen methyl amine compound is simultaneously as alkali compounds.Can be used for alkali compounds of the present invention be not limited to above-mentioned those, do not having can to use any alkali compounds under the situation of specific limited.Described alkali compounds can use separately or two or more are used in combination.
In above-mentioned alkali compounds, preferably methylamine, ethamine, propylamine, butylamine, monoethanolamine, N-methylethanolamine, N-ehtylethanolamine, diethanolamine, isopropanolamine, 2-(2-amino ethoxy) ethanol, ethylene diamine, trimethylene diamine, butylene diamine, diethylene triamine, piperazine and morpholine.
Organic solvent is not particularly limited, as long as miscible with oxygen methyl amine compound.The preferred water-miscible organic solvent that uses.Its example comprises ether solvents such as ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, TC, diethylene glycol single-butyl ether, propylene glycol monomethyl ether, propylene glycol list ethylether, propylene glycol single-butyl ether, DPGME, dihydroxypropane single-ethyl ether, dipropylene glycol single-butyl ether, diethylene glycol dimethyl ether and dipropylene glycol dimethyl ether; Amide solvent such as formamide, monomethyl formamide, dimethyl formamide, single ethyl-formamide, diethylformamide, acetamide, monomethyl acetamide, dimethyl acetamide, single ethyl acetamide, diethyl acetamide, N-Methyl pyrrolidone and N-ethyl pyrrolidone; Alcoholic solvent such as methyl alcohol, ethanol, isopropyl alcohol, ethylene glycol and propylene glycol; Sulfoxide solvent such as dimethyl sulfoxide; Sulfoxide solvent such as dimethyl sulfone, diethyl sulfone, two (2-hydroxyl) sulfone and tetramethylene sulfone; The imidazolone solvent is as 1,3-dimethyl-2-imidazolone, 1,3-diethyl-2-imidazolone and 1,3-diisopropyl-2-imidazolone; And interior ester solvent such as gamma-butyrolacton and δ-Wu Neizhi.
In the above-mentioned solvent, be preferably dimethyl sulfoxide, N, dinethylformamide, N, N-dimethyl acetamide, N-Methyl pyrrolidone, diethylene glycol monomethyl ether, diethylene glycol single-butyl ether, DPGME, dipropylene glycol single-butyl ether and propylene glycol, this is because they obtain and the boiling point height easily.
Antiseptic can comprise aromatic hydroxy compound, sugar alcohol, triazole compounds and chelate compound.
The example of aromatic hydroxy compound comprises phenol, cresols, xylenols, catechol, tert-butyl group catechol, resorcinol, p-dihydroxy-benzene, 1,2,3,-thrihydroxy-benzene, 1,2,4-benzenetriol, saligenin, p-Hydroxybenzylalcohol, diathesin, p-hydroxyphenylethanol, para-aminophenol ,-amino-phenol, diaminophenol, aminoresorcinol, P-hydroxybenzoic acid, septichen, 2,4-dihydroxy-benzoic acid, 2,5-dihydroxy-benzoic acid, 3,4-dihydroxy-benzoic acid, 3,5-dihydroxy-benzoic acid and gallic acid.
The example of sugar alcohol comprises sorbierite, xylitol and palatinit.The example of triazole compounds comprises benzotriazole, aminotriazole(ATA) and Aminotetrazole.
The example of chelate compound comprises phosphate cpd as 1,2-propanediamine tetramethylene phosphoric acid and hydroxyl ethane phosphoric acid; Carboxylic acid such as ethylene diaminetetraacetic acid, dihydroxyethylglycin, nitrilotriacetic acid, oxalic acid, citric acid, malic acid and tartrate; Amine such as two pyridine, tetraphenylporphyrin, phenanthroline and 2,3-pyridine glycol; Oxime compound such as dimethyl glyoxime and diphenyl glyoxime; And acetylide such as phenylacetylene and 2,5-dimethyl-3-hexin-2,5-glycol.
These compounds can use separately or two or more are used in combination.
Described surfactant can be kation, negative ion, nonionic or amphoteric surfactant.
The concentration of described oxygen methyl amine compound in photoresist lift off composition or cleaning combination is 0.001-100wt%, is preferably 0.01-50wt%.Therefore described oxygen methyl amine compound is as alkali, and described oxygen methyl amine compound can be used to remove photoresist and cleaning separately.
If you are using, the concentration of described alkali compounds is the 0.001-99.999wt% of described photoresist lift off composition or cleaning combination, is preferably 0.1-90wt%.
Concentration to organic solvent is not particularly limited, and can determine according to the viscosity of described photoresist lift off composition or cleaning combination or proportion, etching condition, polishing condition etc.If you are using, described concentration is preferably the 99wt% of described photoresist lift off composition or cleaning combination or lower.
Addition to antiseptic is not particularly limited, and is preferably the 30wt% of described photoresist lift off composition or cleaning combination or lower, more preferably 15wt% or lower.
The optional water that makes.If you are using, its concentration can consider that etching condition and polishing condition determine.Usually this concentration is 50wt% or lower.
Thereby method of removing photoresist of the present invention comprises the photoresist layer that utilizes patterning and removes the step of not crested conductive layer area as the conductive layer on the mask etch substrate, and utilizes the photoresist lift off composition to contact to handle the step of removing remaining photoresist layer after the etching.After etching, if necessary, can carry out polishing.Then, utilize the photoresist lift off composition to remove etch residue.The method that is called polishing here is by burning in oxygen plasma or CO and CO 2Remove the photoresist of forming by organic polymer.
Contacting normally between photoresist lift off composition and remaining photoresist layer and the etch residue carried out 0.1-60 minute to 150 ℃ temperature at normal temperature (about 20 ℃).In order to prevent that substrate material is impacted, described contact temperature is preferably low as far as possible.When using photoresist lift off composition of the present invention, described photoresist can be low to moderate under 70 ℃ or the lower temperature and is removed.After removing photoresist, can carry out drip washing to the substrate after handling with organic solvent such as alcohol or water.
Utilize the substrate after the inventive method is handled to contain semiconductor lead material such as silicon, amorphous silicon, polysilicon, silicon oxide layer, silicon nitride layer, copper, aldary, aluminium, aluminium alloy, gold, platinum, silver, titanium, titanium-tungsten, titanium nitride, tungsten, tantalum, tantalum compound, chromium, chromium oxide, evanohm and indium-tin-oxide (ITO); Semiconducting compound such as gallium-arsenic, gallium-phosphorus and indium-phosphorus; Dielectric substance such as strontium-bismuth-tantalum; And LCD substrate material such as glass.
Describe the present invention in more detail with reference to the following example below, described embodiment should not constitute limitation of the scope of the invention.
Embodiment 1-9 and comparative example 1-2
The PFR-790 resist is coated onto on the substrate with tantalum/glass structure, then described resist is developed.Utilize fluoride to carry out dry etching then and form circuit.Removal is tested formed substrate at resist.
Under 40 ℃, described substrate is immersed in the photoresist lift off composition.Behind scheduled time slot, described substrate is taken out, use water wash, carry out drying by nitrogen blowing, under optical microscope, observe then and determine to remove the needed time of resist.The results are shown in the table 1.
Table 1
Other resist of alkalescence fixed oxygen methyl amination water is removed
Thing (wt%) compound (wt%) is (wt%) time (second) (wt%)
Embodiment 1 EA (40) BDE (0.01) 20 DMAC (39.99) 452-BDE (30) 5 DMAC (65) 603 EDA (40) BDE (0.1) 20 DMAC (39.9) 454 EA (40) DBM (0.1) 15 DGME (44.9) 605 BA (35) BDM (1) 9 DGBE (55) 306 MEA (50) DBM (0.1)-NMP (49.9) 457 EA (35) BDE (0.1) 15 DMAC (44.9) 45
Sorbierite (5) 8 PA (60) BDE (0.1) 20 DMSO (19.9) 309 EA (80) BDE (0.1)-PG (19.9) 30 comparative examples 1 EA (40)-20 DMAC (40) 1502 MEA (50)--NMP (50) 600
Alkali compounds
EA: monoethanolamine
EDA: ethylene diamine
BA: butylamine
MEA: methylethanolamine
PA:1-amino-2-propyl alcohol
Oxygen methyl amine compound
The BDE:(butoxymethyl) diethylamine
DBM: two (butoxymethyl) aminomethane
BDM:(isobutoxy methyl) dimethyl amine
Other
DMAC: dimethyl acetamide
DGME: diethylene glycol monomethyl ether
DGBE: diethylene glycol single-butyl ether
The NMP:N-methyl pyrrolidone
DMSO: dimethyl sulfoxide
PG: propylene glycol
Embodiment 10
On an oxide skin(coating), carry out lamination according to the order of barrier metals layer, Al alloy (Al-Cu) layer and barrier metals layer and prepare the substrate that is used for semiconductor element.Utilize resist layer to carry out dry etching, form the Al alloy lead wire, utilize oxygen plasma to carry out polishing then as mask.Ear shape resist is retained on the sidewall of lead, and streak shape resist is retained on the lead.
Make formed substrate contact 15 minutes with the photoresist lift off composition under 70 ℃, described photoetching compositions is made up of 50wt% monoethanolamine, 5wt% 4-tert-butyl catechol, 0.5wt% (butoxymethyl) diethylamide, 19.5wt% diethylene glycol single-butyl ether and 25wt% water.With isopropyl alcohol drip washing and with after the ultrapure water drip washing, described substrate is carried out drying, under scanning electron microscope (SEM), observe then.The result shows that the resist residue is removed fully and do not find corrosion on lead.
Embodiment 11-17 and comparative example 3-4
At room temperature, will in having each photoresist lift off composition of chemical composition shown in the table 2, soak the schedule time with embodiment 10 employed similar semiconductor element substrates.Then with described substrate with ultrapure water drip washing, drying and under scanning electron microscope (SEM), observe, thereby according to the corrosion situation of its resist removal effect of following grade evaluation and lead.
Photoresist is removed
A: remove fully
B: leave over slightly
C: do not remove
The lead corrosion
A: do not have corrosion
B: on conductive line surfaces, have slightly coarse
C: be corroded
Table 2
Chemical composition (wt%)
Alkali compounds oxygen methyl amine compound water other
Embodiment 11 EA (50) BDE (0.2) 17 NMP (29.8)
CA(3)12 DETA(30) BDE(0.5) 20 DMSO(44.5)
CA(5)13 MEA(65) DBM(0.9) 10 DGBE(24)
BT(0.1)14 PA(65) BDE(1) 18 DGME(14)
BuCA(2)15 EA(30) BDE(0.5) 8 DMSO(56)
TMAH (0.5) sorbierite (5) 16 EA (30) EEA (2) 26 DPME (40)
KA (2) 17 AEE (62.5) DBM (0.5) 30 xylitol (5)
KA (2) comparative example 3 EA (50)-17 NMP (30)
CA(3)4 HA(30) - 30 NMP(37)
CA(3)
Alkali compounds
EA: monoethanolamine
DETA: diethylene triamine
MEA: methylethanolamine
PA:1-amino-2-propyl alcohol
TMAH: tetramethyl-ammonium oxyhydroxide
AEE: amino ethoxy ethanol
HA: azanol
Oxygen methyl amine compound
The BDE:(butoxymethyl) diethylamine
DBM: two (butoxymethyl) aminomethane
EEA: ethoxyl methyl diethylamine
Other
The NMP:N-methyl pyrrolidone
CA: catechol
DMSO: dimethyl sulfoxide
DGBE: diethylene glycol single-butyl ether
BT: benzotriazole
DGME: diethylene glycol monomethyl ether
The BuCA:4-tert-butyl catechol
KA: citric acid
Embodiment 18-21 and comparative example 5-6
On glass substrate, according to SiO 2The order of layer, low temperature polycrystalline silicon (p-Si) that 400 are thick layer and insulation course forms, and prepares the substrate that is used for thin film transistor (TFT).Utilize the photoresist layer of patterning to make mask low-temperature polycrystalline silicon layer is carried out etching.After etching, the xsect of test substrate as shown in Figure 1.Remove insulation course is partially-etched, contact with the photoresist lift off composition to expose following low temperature silicon layer.
To test substrate under 40 ℃ is immersed in the photoresist lift off composition.At the fixed time, substrate is taken out, use water wash, and nitrogen blowing carries out drying, observation is determined to remove the needed time of resist under optical microscope then.Simultaneously, observe corrosion situation and estimate by following grade.
A: do not have corrosion
B: slightly coarse
C: polysilicon layer is corroded
The results are shown in the table 3.
Table 3
Other resist of alkalescence fixed oxygen methyl amination water is removed corrosion
Thing (wt%) compound (wt%) is (wt%) time (second) (wt%)
Embodiment 18 EA, (70) BDE, (0.05)-DMAC, (29.95) 30 A19 MEA, (50) BDE, (0.1) 5 DMSO, (44.9) 60 A20 DMEA, (40) BDE, (0.1) 20 DGME, (39.9) 90 A21 DEEA, (30) BDE, (0.1) 24.9 TGDM, (40) 30 A
HA (5) comparative example 5 EA (70)--DMAC (30) 90 C6 MEA (50)--DMSO (50) 180 B
Alkali compounds
EA: monoethanolamine
MEA: methylethanolamine
DMEA:N, the N-dimethylethanolamine
DEEA: DEAE diethylaminoethanol
HA: azanol
Oxygen methyl amine compound
The BDE:(butoxymethyl) diethylamine
Other
DMAC: dimethyl acetamide
DMSO: dimethyl sulfoxide
DGME: diethylene glycol monomethyl ether
TGDM: triethylene glycol dimethyl ether
Embodiment 22
Synthetic (2-methoxyl-2-ethoxy ethoxy methyl) diethylamide
At sal tartari (60g) when existing, under stirring condition, to diethylamide (40.0g, 0.548mol) add 30% formalin (73.1g, 0.731mol) and diethylene glycol monomethyl ether (87.7g, 0.731mol).
After 19 hours, utilize separating funnel to extract oil ingredient, utilize sal tartari (5g) drying, under about 1mmHg and 87 ℃, distill, obtain the title compound of colourless liquid.Its productive rate is 56%.Utilize 1H-NMR (solvent: CDCl 3Concentration: 5%; Reference: TMS; Temperature: room temperature) confirm its chemical constitution.NMR is illustrated among Fig. 2.
Title compound is the water-soluble liquid with weak amine smell.
Embodiment 23
Synthetic (2-methoxyl-2-ethoxy ethoxy methyl) dimethyl amine
According to the mode identical with embodiment 22, repeat reaction, just diethylamide is become dimethyl amine.After the reaction,, obtain title compound by hexane extraction, distillation and purifying.Its productive rate is 10%.Title compound is the water-soluble liquid with weak amine smell.
Embodiment 24
Synthetic (2-methoxyl-1-methyl ethoxy methyl) diethylamide
According to the mode identical with embodiment 22, repeat reaction, just diethylene glycol monomethyl ether is become the methoxyl isopropyl alcohol.After the reaction,, obtain title compound by hexane extraction, distillation and purifying.Its productive rate is 40%.
Comparative example 7
Synthetic diethyl (butoxymethyl) amine
According to G.M.Robinson, R.Robinson, J.Chem.Soc., the method described in 123,523 (1923) is synthesized.Formed amine and moisture from after have very strong amine flavor.
Embodiment 25-29 and comparative example 8-10
According to embodiment 18-21 and the identical mode of comparative example 5-6, the resist of polysilicon is removed and the corrosion situation is estimated.The results are shown in the table 4.
Table 4
Other resist of alkalescence fixed oxygen methyl amination water is removed corrosion
Thing (wt%) compound (wt%) is (wt%) time (second) (wt%)
Embodiment 25 EA, (70) MEEA, (0.05)-DMSO, (29.95) 30 A26 MEA, (10) MEEA, (0.1) 5 DMAC, (84.9) 60 A27-MEMA, (40) 20 DGME, (40) 90 A28 DEEA, (30) MEEA, (0.1) 24.9 TGDM, (40) 30 A
HA, (5) 29-MEEA, (100)--30 A comparative example 8 EA, (70)--DMSO, (30) 90 A9 MEA, (10)--DMAC, (90) 180 C10 DMEA, (40)-20 DGME, (40) 360 B
Alkali compounds
EA: monoethanolamine
MEA: methylethanolamine
DEEA: DEAE diethylaminoethanol
HA: azanol
DMEA:N, the N-dimethylethanolamine
Oxygen methyl amine compound
MEEA:(2-methoxyl-2-ethoxy ethoxy methyl) diethylamide
MEMA:(2-methoxyl-2-ethoxy ethoxy methyl) dimethyl amine
Other
DMSO: dimethyl sulfoxide
DMAC: dimethyl acetamide
DGME: diethylene glycol monomethyl ether
TGDM: triethylene glycol dimethyl ether
Utilize photoresist lift off composition of the present invention, can remove photoresist at short notice at an easy rate conductor material etc. not being caused under the situation of corrosion.Particularly, R wherein 1Be the oxygen methyl amine compound lighter odor of the substituent general formula 1 that contains ehter bond, and be water miscible, and can be by cheap initiation material preparation.The cleaning combination or the photoresist lift off composition that contain this oxygen methyl amine compound can be removed photoresist at short notice conductor material etc. not being caused under the situation of corrosion.

Claims (21)

1. photoresist lift off composition that contains at least a oxygen methyl amine compound, described oxygen methyl amine compound have the alkoxy methyl amine structure or are contained the alkoxy methyl amine structure that the substituting group of ehter bond replaces.
2. the photoresist lift off composition of claim 1, wherein oxygen methyl amine compound is by following general formula 1 expression:
Figure A0312007600021
R wherein 1For alkyl, hydroxyalkyl, aryl, acyl group, alkoxyalkyl, aminoalkyl or contain the substituting group of ehter bond; R 2Be hydrogen, alkyl, acyl group, hydroxyalkyl, aryl, allyl, aminoalkyl, alkoxyalkyl, hydroxyl or amino; R 3Be hydrogen, alkyl, acyl group, hydroxyalkyl, aryl, allyl, aminoalkyl, alkoxyalkyl, hydroxyl or amino, suppose and work as R 2And R 3When being group with 1-8 carbon atom, R 2And R 3And and R 2And R 3The N that links to each other can form ring texture together.
3. claim 1 or 2 photoresist lift off composition, the R in its formula of 1 1Be alkyl, hydroxyalkyl or alkoxyalkyl.
4. claim 1 or 2 photoresist lift off composition, the oxygen methyl amine compound that wherein has an alkoxy methyl amine structure that the substituting group that contained ehter bond replaces are by following general formula 7 expressions:
Figure A0312007600022
R wherein 2And R 3As hereinbefore defined; R 4For having the alkyl of 1-8 carbon atom; R 5For having the alkylidene of 1-4 carbon atom; And n is the integer of 1-4; Suppose when n is the integer of 2-4 2-4 R 5Group can be identical or different.
5. the photoresist lift off composition of claim 4, wherein oxygen methyl amine compound is by following general formula 8 expressions:
Figure A0312007600031
R wherein 2, R 3And R 4As hereinbefore defined.
6. the photoresist lift off composition of claim 4, wherein oxygen methyl amine compound is by following general formula 9 expressions:
Figure A0312007600032
R wherein 2, R 3And R 4As hereinbefore defined.
7. any one photoresist lift off composition among the claim 1-6 further contains alkali compounds.
8. the photoresist lift off composition of claim 7, wherein alkali compounds is at least a compound that is selected from alkyl amine, alkanolamine, polyamines, azanol, cyclammonium and tetraethanolammonium hydroxide.
9. any one photoresist lift off composition among the claim 1-8 further contains organic solvent.
10. any one photoresist lift off composition among the claim 1-9 further contains antiseptic.
11. the photoresist lift off composition of claim 10, antiseptic wherein are at least a compound that is selected from aromatic hydroxy compound, sugar alcohol, triazole compounds and huge legendary turtle combination compound.
12. any one photoresist lift off composition among the claim 1-11 further contains water.
13. the photoresist lift off composition of claim 7 or 8 wherein contains 0.001-99.999wt% oxygen methyl amine compound and 0.001-99.999wt% alkali compounds.
14. a method of removing photoresist is included in and forms the step of removing remaining photoresist behind the lead on the substrate that is used for semiconductor element or liquid crystal display cells.
15. oxygen methyl amine compound by following general formula 7 expressions:
R 2Be hydrogen, alkyl, acyl group, hydroxyalkyl, aryl, allyl, aminoalkyl, alkoxyalkyl, hydroxyl or amino; R 3Be hydrogen, alkyl, acyl group, hydroxyalkyl, aryl, allyl, aminoalkyl, alkoxyalkyl, hydroxyl or amino, suppose and work as R 2And R 3When being group with 1-8 carbon atom, R 2And R 3And and R 2And R 3The N that links to each other can form ring texture together; R 4For having the alkyl of 1-8 carbon atom; R 5For having the alkylidene of 1-4 carbon atom; And n is the integer of 1-4; Suppose when n is the integer of 2-4 2-4 R 5Group can be identical or different.
16. the oxygen methyl amine compound of claim 15, described oxygen methyl amine compound is represented by following general formula 8:
R wherein 2, R 3And R 4As hereinbefore defined.
17. the oxygen methyl amine compound of claim 15, described oxygen methyl amine compound is represented by following general formula 9:
Figure A0312007600042
R wherein 2, R 3And R 4As hereinbefore defined.
18. the oxygen methyl amine compound of claim 15 or 16, described oxygen methyl amine compound is represented by following general formula 4:
Figure A0312007600043
19. the oxygen methyl amine compound of claim 15 or 17, described oxygen methyl amine compound is represented by following general formula 5:
20. a cleaning combination that is used for semiconductor element contains at least a by any defined oxygen methyl amine compound among the claim 15-19.
21. photoresist lift off composition that contains at least a by any defined oxygen methyl amine compound among the claim 15-19.
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KR20040002455A (en) 2004-01-07
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